22. Arthur Crandall & Gabbo

For years, Krusty the Clown was the only act in town. Despite being a vulgar, illiterate alcoholic, he had a legion of fans across Springfield and was filthy rich because of it. But as his act started to wear thin, he was challenged by a rival kid’s TV show host who won the hearts of Springfield's citizens everywhere: Arthur Crandall and his puppet Gabbo.

Armed with a catchy theme song and a hackneyed catchphrase (“I’m a bad little boy”), Gabbo was soon the flavor of the month and he put Krusty out of business in the process. But Crandall’s time quickly ran out when Gabbo called all the kids of Springfield “Little S.O.B’s” live on the air. This is one of the great episodes in the show’s history, and much of that has to do with the spectacular flame-out of Crandall and his foul-mouthed puppet.